NP-MRD: Showing NP-Card for methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate (NP0302326)

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Record Information

Version

2.0

Created at

2022-09-10 15:48:19 UTC

Updated at

2022-09-10 15:48:19 UTC

NP-MRD ID

NP0302326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate

Description

Methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]Heptadec-8-ene-9-carboxylate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate is found in Erythropodium caribaeorum. Methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]Heptadec-8-ene-9-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201500492D          

 42 44  0  0  0  0            999 V2000
    5.5620    6.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    5.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7961    4.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0996    5.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    4.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4578    3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4231    2.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0124    2.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6454    1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0275    0.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7232    1.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2519    0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6919    2.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0046    1.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9954    2.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    2.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0469    1.5437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9457    0.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642    2.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    1.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983    1.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8018    1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365    2.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    2.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    1.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    2.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677    2.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    3.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    3.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337    4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    3.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9060    4.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407    4.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2443    5.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6719    5.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4635    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7323    0.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6976   -0.8037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359    0.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 23 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
M  END

     RDKit          3D

 82 84  0  0  0  0  0  0  0  0999 V2000
   -5.7574    1.8932   -3.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9800    0.9930   -2.8134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4116    1.4464   -1.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930    2.6324   -1.3177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915    0.5869   -0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3695   -0.6741   -1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -1.7722   -0.5071 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8748   -2.1502    0.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -3.4303    0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331   -4.3570    1.7283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3426   -3.4946   -0.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1640   -4.3065   -0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863   -1.9733   -0.5791 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7135   -1.9672   -1.8723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810   -1.3346    0.4428 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2300   -2.3360    1.2879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248   -2.4873    2.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347   -3.5377    3.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364   -1.7282    3.2048 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6965   -0.3487    0.1752 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9487   -0.9328   -0.3734 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5779   -1.9341    0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0980    0.0110   -0.5821 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1341   -0.6382   -1.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4081   -0.7103   -0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5284   -1.3934   -1.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6324   -0.1732    0.3485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6319    1.2516   -1.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201    1.8386   -0.3386 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2709    3.1048   -0.8609 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5315    4.3006   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1022    5.5805   -0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    4.3427    0.8438 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    1.0135   -0.3181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0830    1.0631   -1.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5676    1.7985    0.6211 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6727    1.2530    1.9139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920    1.8633    3.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4305    1.2333    4.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020    3.0374    2.9624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101    2.1986    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0617    1.3209    0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1980    2.2588   -4.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1160    2.7485   -2.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6781    1.3705   -3.9606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8896   -0.9030   -2.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1573   -2.7145   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -3.8201   -1.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6308   -3.9484   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317   -4.5670    0.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101   -5.3325   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528   -1.5833   -2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854   -0.8617    1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0602   -4.4826    3.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5361   -3.3280    4.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -3.6939    3.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0279   -0.0899    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8145   -1.4610   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135   -1.5681    1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2347   -2.9693    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6946   -2.0172    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690    0.3619    0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5472   -2.4718   -1.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4507   -1.2472   -2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4833   -0.9594   -1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3979    1.1966   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5119    1.9672   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0826    1.9282    0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1914    5.5141   -2.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289    5.7898   -0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6822    6.4433   -0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1062    2.0987   -2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5983    0.3875   -2.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0853    0.7468   -2.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1005    2.8226    0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.4612    4.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4386    0.7837    4.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695    1.9714    5.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2208    3.2414    0.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    2.3607   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    1.8877    0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7680    0.5954    1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 29 34  1  0
 34 35  1  6
 34 36  1  0
 36 41  1  0
 41 42  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 42  5  1  0
 13  7  1  0
 34 20  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  6 46  1  0
  7 47  1  6
 11 48  1  6
 12 49  1  0
 12 50  1  0
 12 51  1  0
 14 52  1  0
 15 53  1  1
 18 54  1  0
 18 55  1  0
 18 56  1  0
 20 57  1  1
 21 58  1  6
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  1
 28 66  1  0
 28 67  1  0
 29 68  1  1
 32 69  1  0
 32 70  1  0
 32 71  1  0
 35 72  1  0
 35 73  1  0
 35 74  1  0
 36 75  1  1
 41 79  1  0
 41 80  1  0
 42 81  1  0
 42 82  1  0
 39 76  1  0
 39 77  1  0
 39 78  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
M  END


  Mrv1533004201500492D          

 42 44  0  0  0  0            999 V2000
    5.5620    6.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    5.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7961    4.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0996    5.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614    4.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4578    3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4231    2.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0124    2.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6454    1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0275    0.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7232    1.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2519    0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6919    2.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0046    1.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9954    2.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    2.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0469    1.5437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9457    0.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2642    2.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    1.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4983    1.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8018    1.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365    2.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    2.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4089    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3741    1.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    2.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677    2.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    3.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025    3.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3337    4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    3.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9060    4.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407    4.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2443    5.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6719    5.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4635    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7323    0.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6976   -0.8037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359    0.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 23 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC2OC(=O)C(C)C2(O)C(OC(C)=O)C2C(C)C(CC(OC(C)=O)C2(C)C(CC1)OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O13/c1-13-20(38-15(3)30)12-22(40-17(5)32)28(7)21(39-16(4)31)10-9-19(27(35)37-8)11-23-29(36,14(2)26(34)42-23)25(24(13)28)41-18(6)33/h11,13-14,20-25,36H,9-10,12H2,1-8H3

> <INCHI_KEY>
VXLRUARRHGRFLY-UHFFFAOYSA-N

> <FORMULA>
C29H40O13

> <MOLECULAR_WEIGHT>
596.626

> <EXACT_MASS>
596.246891348

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.16827247687059

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
0.9494404043333325

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.359339004693798

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9538251193469316

> <JCHEM_POLAR_SURFACE_AREA>
178.02999999999997

> <JCHEM_REFRACTIVITY>
140.51889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      10.382  11.297   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.318   9.759   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.953   9.046   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.653   9.871   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.888   7.507   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.188   6.682   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.123   5.143   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.223   4.065   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.538   2.686   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.251   1.321   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.817   2.821   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.937   1.811   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.758   4.430   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.475   3.578   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.458   5.255   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.921   3.812   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.902   2.625   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.421   2.882   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.365   1.182   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.093   4.542   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.028   3.003   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.328   2.178   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.663   2.290   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.363   3.116   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.428   4.654   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.128   5.480   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.763   4.767   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.698   3.228   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.537   5.592   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.793   5.368   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.493   6.193   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.858   6.906   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.223   7.619   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.523   6.794   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.558   7.732   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.623   9.270   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.323  10.096   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.988   9.983   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.599   0.752   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.234   0.038   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.169  -1.500   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.934   0.864   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   30                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   39                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   20   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33    5                                                       
CONECT   35   32   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   23   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0,]heptadec-8-ene-9-carboxylic acid	Generator
Methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylic acid	Generator

Chemical Formula

C₂₉H₄₀O₁₃

Average Mass

596.6260 Da

Monoisotopic Mass

596.24689 Da

IUPAC Name

methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate

Traditional Name

methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2OC(=O)C(C)C2(O)C(OC(C)=O)C2C(C)C(CC(OC(C)=O)C2(C)C(CC1)OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C29H40O13/c1-13-20(38-15(3)30)12-22(40-17(5)32)28(7)21(39-16(4)31)10-9-19(27(35)37-8)11-23-29(36,14(2)26(34)42-23)25(24(13)28)41-18(6)33/h11,13-14,20-25,36H,9-10,12H2,1-8H3

InChI Key

VXLRUARRHGRFLY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Erythropodium caribaeorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Hexacarboxylic acid or derivatives
Briarane diterpenoid
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.86	ALOGPS
logP	0.95	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	178.03 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	140.52 m³·mol⁻¹	ChemAxon
Polarizability	59.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73817252

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate (NP0302326)

MOL for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

3D MOL for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

3D SDF for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

3D-SDF for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

PDB for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

3D PDB for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

SMILES for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

INCHI for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

Structure for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)

3D Structure for NP0302326 (methyl 2,12,14,16-tetrakis(acetyloxy)-3-hydroxy-4,13,17-trimethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadec-8-ene-9-carboxylate)